Native bees provide the majority of pollination services to wild and cultivated flowering plants. Unfortunately, as the area of modern agriculture expands, fragmenting and destroying natural habitat, the persistence of native bees and the pollination services they provide is threatened. With the current decline in managed bees, understanding how local management decisions and landscape factors influence native bees and their contribution to crop pollination becomes more urgent. Using Wisconsin cranberry as a model system, I examined the pollination requirements of cranberry, the contribution of bees to pollination, and the influence of local and landscape factors on native bees. I further investigated the barriers to farmer adoption of on-farm conservation programs for native bees. Contrary to previous studies, I found that non-biotic factors contribute significantly to cranberry pollination (chapter 1). My research demonstrates that, even in the absence of bees, cranberry is able to produce fruit. Fruit production was, however, increased when bees were present supporting the practice of using honey bees for pollination. At a farm scale, cranberry yield was positively correlated with an increasing stocking density of honey bee hives, but only at farms located in low-woodland landscapes (chapter 2). When honey bees were absent, all farms had significant yield, but those in high woodland landscapes had a marginally higher yield than farms in low woodland landscapes. Farms in high woodland landscapes also had a higher abundance and richness of native bees although there was only a weak relationship between native bees and yield (chapter 3). The contribution of bees to cranberry pollination increased with increasing flowering upright density, suggesting that local management can enhance the contribution by bees. Additional results indicate that cranberry growers are interested in creating pollinator habitat on their farms but are limited by a lack of technical support and perceived time and financial commitments (chapter 4). This dissertation contributes to our understanding of cranberry pollination biology and how local and landscape factors influence bees and their contribution to yield. I provide practical guidelines for growers on pollination management for cranberry and for conservation professionals on increasing cranberry grower participation in federal pollinator conservation programs.